2- chloroethyl isocyanate

The reaction of 2-amino-5-nitrothiazole with (3-chloroethyl isocyanate gives the corresponding thiazolyl urea (137) (Scheme 90) (298). Other examples are given in Section V.l.B, where the preparation of thiazolyl-thioureas is discussed,... 

Reaction of 4-cyano-3-imino-2,3,5,6,7,8-hexahydro-l//-pyrido[l,2-c]pyr-imidin-l-one 169 with 2-chloroethyl isocyanate at ambient temperature and under reflux gave N-acylated 170 and tetracyclic derivative 171, respectively (95MI1). Similar reaction of 3-amino-4-cyano-2,4a5,6,7,8-hexahydro-l// pyrido[l,2-c]pyrimidin-1-ones 172 afforded tricyclic compounds 173. 

Finally, ortho aminoesters have been used to produce 7-deazaxanthines. For example ethyl 2-amino-5-phenyl-l//-pyrrole-3-carboxylate is first treated with 2-chloroethyl isocyanate in refluxing toluene. The resulting urea derivative is then allowed to react with l-(2-methoxyphenyl)piperazine and cyclized to the expected pyrrolo[2,3-,7 pyrimidin-2,4(177,377)-dione <2006BMCL150>. 

Arylpiperazinylethylthieno[3,2-d]pyrimidinediones 209 were obtained from o-aminoester 189 (R2 = R3 = H, Y = Me) in three steps. The latter was reacted with 2-chloroethyl isocyanate to give the 2-chloroethylurea 207. This urea was then treated with various phenyl-substituted piperazines to afford ureas 208. These ureas were cyclized to the thienopyrimidinedi-ones 209 by heating in methanolic potassium hydroxide (88JMC1786). 

Press et al. (87USP4670560 88JMC1786) reacted aminoesters 292 with 2-chloroethyl isocyanate in refluxing toluene and obtained the 2-chloroethylureas 304. These ureas were further reacted with various N-phenyl-substituted piperazines in either THF or propan-2-ol and in the presence of sodium iodide and sodium bicarbonate. The resulting substituted ureas 305 were then heated in methanolic potassium hydroxide to afford the thieno[3,4-d]pyrimidinediones 306. 

Treatment of the sodium salt of 2-cyanocyclododecanone (VII/109) with a>-haloisocyanates yields the 14-membered imide VII/U2. Two cyclization products of VII/112 were obtained in the presence of potassium carbonate as base. In the C-alkylated bicycle, VII/113, the central bridge bond is solvolyzed to form the 16-membered amide VII/114. The O-alkylated bicycle, VII/US, which is the minor product, was not investigated further. When 2-chloroethyl isocyanate was used as reagent, the analogue of VII/115 was formed directly. Because of its multistepcharacter the reaction resembles MIMIRC (Scheme VII/9) [59] [60]. 

CHLOROETHYLIDENE FLUORIDE see CFX250 a-CHLOROETHYUDENE FLUORIDE see CFX250 2-CHLOROETHYL ISOCYANATE see IKHOOO CHLOROETHYL MERCURY see CHC500 2-CHLOROETHYL METHANESULFONATE see CHC750... 

N-(2-Chloroethyl)-N-nitroso ureas are an active class of antitumor agents, which are usually obtained by nitrosa-tion of the previously prepared urea. Because of difficulties in achieving regioselective nitrosation, several authors have suggested alternatives processes. Unfortunately, the starting materials proposed are either unstable such as carbamoyl azides (Ref. 199) or extremely toxic such as the 2-chloroethyl isocyanate (Ref. 200). 

This phosgene-pyridine salt can react with other amines. For example, with aziridine, a stoicheiometric amount of pyridine is displaced to produce pyridinium chloride and equimolar amounts of pyridine and 2-chloroethyl isocyanate [2042b]. 

Finally, in an intriguing reaction, phosgene reacts with 2-aziridinyl-2-oxazoline to form the trimer of 2-chloroethyl isocyanate [2042a] ... 

MR Davis, K Kassahun, CM Jochheim, KM Brandt, TA Baillie. Glutathione and A-acetylcysteine conjugates of 2-chloroethyl isocyanate. Identification as metabolites of N,N -bis(2-chloroethyl)-A-nitrosourea in the rat and inhibitory properties toward glutathione reductase in vitro. Chem Res Toxicol 6 376, 1993. 

Chlorodecarbomethoxylation, 480 Chlorodicarbonylrhodium(l) dimer, 108 Chlorodiphenylmethylium hexachloro-antimonate, 108-109 a-Chloroepoxy ketones, 354-355 Chlorofluorocyclopropanes, 511 Chlorofluorocarbene, 175, 511 /3-Chloroethyl isocyanate, 570 Chloroformates, 226 a-Chloroglycidic esters, 353 6-Chloro-N-hydroxybenzotriazole, 106... 

When equivalent amounts of aziridine and triethylamine in tetrachloromethane are added to a solution containing 1 equiv. of phosgene at —10 °C, a mixture of bis(aziridinyl)urea 173 and 2-chloroethyl isocyanate 174 is formed, the former being the major product [109]. 

Chloroethyl isocyanate 174 is the major product obtained when aziridine is allowed to react with an equivalent amount of 1 1 triethylamine-phosgene complex 175 [108] or 2 1 pyridine-phosgene complex 177 [109]. Aziridine carbamoyl chloride 176 was postulated as a transient intermediate in this reaction. Attempts to trap this elusive species as the triethylammonium or pyridinium salt have been unsuccessfiil [109]. 

Treatment of per-O-acetylated glycosylamines with 2-chloroethyl isocyanate, followed by nitrosation (sodium nitrite in formic acid) and deacetylation, yielded a series of (2-chloroethyl)nitrosourea derivatives [e.g. l-(2-chloroethyl)-3-(j3-D-gIucopyranosyl)-l-nitrosourea (150)], which showed remarkable anti-... 

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